JPS6136509B2 - - Google Patents

Info

Publication number: JPS6136509B2
Authority: JP; Japan
Prior art keywords: acid; naphthylamine; reaction; alcohol; weight
Prior art date: 1977-07-16
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP53085255A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5419954A (en

Inventor

Shesuraa Birii

Beere Horusuto

Pyuutaa Rorufu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-07-16

Filing date

1978-07-14

Publication date

1986-08-19

1978-07-14 Application filed by Bayer AG filed Critical Bayer AG

1979-02-15 Publication of JPS5419954A publication Critical patent/JPS5419954A/ja

1986-08-19 Publication of JPS6136509B2 publication Critical patent/JPS6136509B2/ja

Status Granted legal-status Critical Current

Links

OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
239000002253 acid Substances 0.000 claims description 65
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
UBDHSURDYAETAL-UHFFFAOYSA-N 8-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 UBDHSURDYAETAL-UHFFFAOYSA-N 0.000 claims description 39
150000003839 salts Chemical class 0.000 claims description 39
238000006243 chemical reaction Methods 0.000 claims description 33
239000000203 mixture Substances 0.000 claims description 32
APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 claims description 31
238000000034 method Methods 0.000 claims description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
229910052751 metal Inorganic materials 0.000 claims description 20
239000002184 metal Substances 0.000 claims description 20
239000011541 reaction mixture Substances 0.000 claims description 20
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 17
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 10
238000004821 distillation Methods 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
230000020477 pH reduction Effects 0.000 claims 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
235000002639 sodium chloride Nutrition 0.000 description 34
239000000243 solution Substances 0.000 description 20
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 11
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 7
150000001298 alcohols Chemical class 0.000 description 7
230000035484 reaction time Effects 0.000 description 7
HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
229910052500 inorganic mineral Inorganic materials 0.000 description 6
235000010755 mineral Nutrition 0.000 description 6
239000011707 mineral Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
-1 alkali metal salts Chemical class 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
NDYYJXGERWTRSD-UHFFFAOYSA-N 4-aminonaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 NDYYJXGERWTRSD-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
229910052759 nickel Inorganic materials 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 4
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 3
YOPRSDZTTFFTDQ-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-n-(2-chloropyridin-3-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound CC=1ON=C(C=2C(=CC=CC=2F)Cl)C=1C(=O)NC1=CC=CN=C1Cl YOPRSDZTTFFTDQ-UHFFFAOYSA-N 0.000 description 3
JQIUQZOYSRHTBE-UHFFFAOYSA-N 4-nitronaphthalene-1,2,3-trisulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(S(O)(=O)=O)C(S(=O)(=O)O)=C([N+]([O-])=O)C2=C1 JQIUQZOYSRHTBE-UHFFFAOYSA-N 0.000 description 3
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
238000005904 alkaline hydrolysis reaction Methods 0.000 description 3
GPUMPJNVOBTUFM-UHFFFAOYSA-N naphthalene-1,2,3-trisulfonic acid Chemical class C1=CC=C2C(S(O)(=O)=O)=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC2=C1 GPUMPJNVOBTUFM-UHFFFAOYSA-N 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
150000002828 nitro derivatives Chemical class 0.000 description 3
FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
238000007086 side reaction Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
HKTWHHAJDJCUPC-UHFFFAOYSA-N 7-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 HKTWHHAJDJCUPC-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
VEUACKUBDLVUAC-UHFFFAOYSA-N [Na].[Ca] Chemical compound [Na].[Ca] VEUACKUBDLVUAC-UHFFFAOYSA-N 0.000 description 2
239000003929 acidic solution Substances 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
238000007865 diluting Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000011874 heated mixture Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
230000000802 nitrating effect Effects 0.000 description 2
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 2
229910052939 potassium sulfate Inorganic materials 0.000 description 2
235000011151 potassium sulphates Nutrition 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000010959 steel Substances 0.000 description 2
150000005846 sugar alcohols Polymers 0.000 description 2
NJPKYOIXTSGVAN-UHFFFAOYSA-K trisodium;naphthalene-1,3,6-trisulfonate Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(S([O-])(=O)=O)=CC2=CC(S(=O)(=O)[O-])=CC=C21 NJPKYOIXTSGVAN-UHFFFAOYSA-K 0.000 description 2
238000005406 washing Methods 0.000 description 2
GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 1
NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical compound CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 description 1
238000006887 Ullmann reaction Methods 0.000 description 1
QCGGXGCODUUTLZ-UHFFFAOYSA-N [Na].[Na].[Na].[Na] Chemical compound [Na].[Na].[Na].[Na] QCGGXGCODUUTLZ-UHFFFAOYSA-N 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
150000002505 iron Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
231100000957 no side effect Toxicity 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000001120 potassium sulphate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
KSGAYRCFZRBMFA-UHFFFAOYSA-K trisodium;8-nitronaphthalene-1,3,6-trisulfonate Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(S([O-])(=O)=O)=C2C([N+](=O)[O-])=CC(S([O-])(=O)=O)=CC2=C1 KSGAYRCFZRBMFA-UHFFFAOYSA-K 0.000 description 1
SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical class [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B34/00—Obtaining refractory metals
- C22B34/10—Obtaining titanium, zirconium or hafnium
- C22B34/12—Obtaining titanium or titanium compounds from ores or scrap by metallurgical processing; preparation of titanium compounds from other titanium compounds see C01G23/00 - C01G23/08

Landscapes

Engineering & Computer Science (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Environmental & Geological Engineering (AREA)
General Life Sciences & Earth Sciences (AREA)
Geology (AREA)
Manufacturing & Machinery (AREA)
Materials Engineering (AREA)
Mechanical Engineering (AREA)
Metallurgy (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP8525578A 1977-07-16 1978-07-14 Production of monoalkali metal salt of 11aminoo 88naphtoll3*66 disulfonic acid Granted JPS5419954A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772732291 DE2732291A1 (de)	1977-07-16	1977-07-16	Verfahren zur herstellung von 1-amino-8-naphthol-3,6-disulfonsaeure (h-saeure)

Publications (2)

Publication Number	Publication Date
JPS5419954A JPS5419954A (en)	1979-02-15
JPS6136509B2 true JPS6136509B2 (zh)	1986-08-19

Family

ID=6014143

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP8525578A Granted JPS5419954A (en)	1977-07-16	1978-07-14	Production of monoalkali metal salt of 11aminoo 88naphtoll3*66 disulfonic acid

Country Status (6)

Country	Link
US (1)	US4178308A (zh)
EP (1)	EP0000493B1 (zh)
JP (1)	JPS5419954A (zh)
BR (1)	BR7804546A (zh)
DE (2)	DE2732291A1 (zh)
IT (1)	IT1105430B (zh)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2716030C3 (de) *	1977-04-09	1981-07-16	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von Monoalkalisalzes der 1-Amino-8-naphthol-3,6-disulfonsäure
US4325889A (en) *	1978-08-04	1982-04-20	Bayer Aktiengesellschaft	Process for the preparation of 1-amino-8-naphthol-3,6-disulphonic acid (H-acid)
DE2843680A1 (de) *	1978-10-06	1980-04-24	Bayer Ag	Verfahren zur herstellung von 1-amino-8-naphthol-4,6-disulfonsaeure (k-saeure)
DE3118147A1 (de)	1981-05-07	1982-12-02	Bayer Ag, 5090 Leverkusen	Verfahren zur isolierung von h-saeure und k-saeure
CN1057521C (zh) *	1997-08-16	2000-10-18	吉林化学工业股份有限公司染料厂	1－氨基－8－奈酚－3.6二磺酸单钠盐生产工艺的改进
JP2011516833A (ja)	2008-03-21	2011-05-26	アボット・ポイント・オブ・ケア	蛍光消光及び／又は蛍光退色を用いて個々の細胞又は粒状物質を分析するための方法及び装置
US7903241B2 (en)	2008-03-21	2011-03-08	Abbott Point Of Care, Inc.	Method and apparatus for determining red blood cell indices of a blood sample utilizing the intrinsic pigmentation of hemoglobin contained within the red blood cells
CA2719004C (en)	2008-03-21	2013-06-18	Abbott Point Of Care, Inc.	Method and apparatus for determining a focal position of an imaging device adapted to image a biologic sample
ES2560098T3 (es)	2008-03-21	2016-02-17	Abbott Point Of Care, Inc.	Método y aparato para detectar y contar plaquetas individualmente y en agregados
CN102807513B (zh) *	2012-08-23	2013-12-18	楚源高新科技集团股份有限公司	一种利用h酸母液回收生产变色酸钠盐的工艺
CN103113269B (zh) *	2013-01-23	2015-07-22	绍兴奇彩化工有限公司	1,8-二硝基-3,6-萘二磺酸盐加氢还原方法
CN107986997A (zh) *	2017-12-08	2018-05-04	荆门市熊兴化工有限公司	一种用于h酸生产过程中的碱熔方法
CN115201363B (zh) *	2022-07-06	2024-02-09	广东众和高新科技股份公司	一种检测1,8-二氨基-3,6-萘二磺酸含量的液相色谱分析方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US540412A (en) *		1895-06-04		Moritz ulrich and johann bammann
US458286A (en) *		1891-08-25		Werke
US511708A (en) *		1893-12-26		Gesellschaft fur aotlif fabrikation
US1670406A (en) *	1925-05-09	1928-05-22	Newport Co	Process of preparing h-acid
IT1078453B (it) *	1976-06-16	1985-05-08	American Cyanamid Co	Perfezionamento nella sintesi di acido ammino-idrossinaftalene-solfonico
US4130581A (en) *	1977-10-03	1978-12-19	American Cyanamid Company	Preparing J acid by fusion using phenolic fluxing agent

1977
- 1977-07-16 DE DE19772732291 patent/DE2732291A1/de not_active Withdrawn
1978
- 1978-06-28 US US05/920,033 patent/US4178308A/en not_active Expired - Lifetime
- 1978-07-11 DE DE7878100354T patent/DE2857516D1/de not_active Expired
- 1978-07-11 EP EP78100354A patent/EP0000493B1/de not_active Expired
- 1978-07-14 IT IT50300/78A patent/IT1105430B/it active
- 1978-07-14 JP JP8525578A patent/JPS5419954A/ja active Granted
- 1978-07-14 BR BR7804546A patent/BR7804546A/pt unknown

Also Published As

Publication number	Publication date
EP0000493A1 (de)	1979-02-07
DE2732291A1 (de)	1979-02-01
IT1105430B (it)	1985-11-04
US4178308A (en)	1979-12-11
DE2857516D1 (en)	1980-02-14
EP0000493B1 (de)	1980-01-09
IT7850300A0 (it)	1978-07-14
BR7804546A (pt)	1979-03-20
JPS5419954A (en)	1979-02-15

Publication	Publication Date	Title
JPS6136509B2 (zh)	1986-08-19
US4221734A (en)	1980-09-09	Process for the preparation of derivatives of fluoroalkane-carboxylic and perfluoroalkane-sulfinic acids
JPH0469628B2 (zh)	1992-11-06
US4166826A (en)	1979-09-04	Process for the preparation of 1-amino-8-naphthol-3,6-disulphonic acid (H-acid)
US4467123A (en)	1984-08-21	Process for the preparation of alkali metal diphenylates and free hydroxydiphenyls
US4325889A (en)	1982-04-20	Process for the preparation of 1-amino-8-naphthol-3,6-disulphonic acid (H-acid)
JPS58116435A (ja)	1983-07-11	４−ヒドロキシ−２，４，６−トリメチルシクロヘキサ−２，５−ジエン−１−オンの製造法
JPH025741B2 (zh)	1990-02-05
GB1577697A (en)	1980-10-29	Process for the preparation of 1 - amino - 8 - naphthol-3,6-disulphonic acid (h-acid)
US4407762A (en)	1983-10-04	Process for the isolation of 1-naphthylamine-4,8-disulphonic acid
JPS61282355A (ja)	1986-12-12	４，４’−ジニトロスチルベン−２，２’−ジスルホン酸塩の製造法
JP2512532B2 (ja)	1996-07-03	４，４´−ジニトロスチルベン−２，２´−ジスルホン酸の製造方法
US5312974A (en)	1994-05-17	Process for the production of light-colored lower alkane-sulfonic acids, more particularly methanesulfonic acid
US4609503A (en)	1986-09-02	Process for the preparation of 1-amino-8-naphthol-4,6-disulphonic acid (k-acid)
US3410900A (en)	1968-11-12	Production of phenylhydrazine
US4180521A (en)	1979-12-25	Process for the preparation of naphthalene-1,3,6-trisulphonic acid
JPH11152263A (ja)	1999-06-08	酸化による２−カルボキシ−５−ニトロベンゼンスルホン酸およびその塩の製造方法
JPS585905B2 (ja)	1983-02-02	１−アミノ−８−ナフト−ル−３，６−ジスルホン酸（ｈ−酸）の製造方法
US3910995A (en)	1975-10-07	Process for preparing 2,5-dihalo-3-nitrobenzoic acid
JPS58206550A (ja)	1983-12-01	５−アセチル−２−アルキルベンゼンスルホン酸またはその塩の製造法
US4393234A (en)	1983-07-12	Process for the preparation of 3-hydroxybenzoic acid
US6218555B1 (en)	2001-04-17	Process for the preparation of alkanoyloxy-benzenesulfonic acids and salts thereof
JPH06737B2 (ja)	1994-01-05	アルキル―〔３クロロフェニル〕―スルホンの製造方法
US4377535A (en)	1983-03-22	Process for the preparation of nitro-T-acid (8-nitro-naphthalene-1,3,6-trisulphonic acid)
US4987266A (en)	1991-01-22	Process for the manufacture of nitrophenetole